Water → N-(2,4-dichlorophenyl)ethanehydrazonoyl chloride

HRID 1612424Notes

Reaction equation

HRID 1612424 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][N:10]=[C:11]([Cl:13])[CH3:12].[O-:14][C:15]#[N:16].[K+].O>COCCOCCOC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][N:10]=[C:11]([Cl:13])[CH3:12].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:15](=[O:14])[NH:16][C:11]([CH3:12])=[N:10]1

Participants

6

Reactant 3

HCID 962WaterHCID 11378442Potassium cyanateHCID 72815031N-(2,4-dichlorophenyl)ethanehydrazonoyl chloride

Product 2

HCID 72815031N-(2,4-dichlorophenyl)ethanehydrazonoyl chlorideHCID 135477896AG-H-19234

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of 5.1 grams (0.0214 mole) of N-(2,4-dichlorophenyl)ethanehydrazonoyl chloride (A), prepared as in Example 1, 2.1 grams (0.0257 mole) potassium cyanate, and 3 mL of water in 51 mL of diglyme was stirred at ambient temperature for about 22 hours. After this time, the reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in about 500 mL of ethyl acetate and washed with three 25 mL portions of water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was triturated with hexane and the resultant solid was collected by filtration. The solid was dried, yielding 4.5 grams (85.2% yield from (A)) of subject compound (I).

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure to a residue
  2. dissolutionThe residue was dissolved in about 500 mL of ethyl acetate
  3. washwashed with three 25 mL portions of water
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to a residue
  7. customThe residue was triturated with hexane
  8. filtrationthe resultant solid was collected by filtration
  9. customThe solid was dried

Sources & evidence

ORD record
ord-0504acf0541a4497998af35281e9f2fd
Source dataset
uspto-grants-2006_01
Patent number
US06992221B2

Reaction notes

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